This application claims the priority of Japanese Patent applications No. 11-087741 and No. 11-089072 filed on Mar. 30, 1999, and No. 2000-008746 filed on Jan. 18, 2000, which are incorporated herein by reference.
1. Field of the Invention
This invention relates to a antiseptic/antifungal agent and an endermic liniment composition which contains it.
2. The Prior Art
Generally, an endermic liniment composition such as a cosmetic contains an antiseptic/antifungal agent (in the present specifications, xe2x80x9cantisepticxe2x80x9d also means xe2x80x9cantifungalxe2x80x9d unless specified otherwise) such as paraoxy benzoate (so called parabens), salicylic acid, and sorbic acid and/or an antiseptic assistant such as phenoxy ethanol, for the purpose of improving the shelf life of the products by suppressing replication of microorganisms which contaminate the composition from outside and eventually killing off these microorganisms.
Antiseptic components such as paraben and/or antiseptic assistant components such as phenoxy ethanol have superior safety and efficacy when used as an antiseptic component in an endermic liniment composition. However, they still may cause irritation and such to a small number of very sensitive users.
Recently, endermic liniment compositions which are gentler to the skin are more in demand, and therefore the requirements of today""s endermic liniment compositions are very difficult to meet by simply adding these parabens and phenoxy ethanol as the antiseptic components.
Of course it is possible to create an endermic liniment composition which does not have antiseptic components such as parabens or antiseptic assistant components such as phenoxy ethanol. However, in such a case, in order to ensure the antiseptic properties, the amount and/or the expiration date have to be limited or a complex means such as small subdivided containers or the backless mechanism has to be used, resulting in a tendency towards low economic benefits and versatility.
Therefore, the object of the present invention is to provide a new antiseptic agent which has much superior safety and usability and can be blended into endermic liniment compositions, as well as an endermic liniment composition which contains it.
The inventors conducted earnest research to achieve the aforementioned object, and, as a result, discovered that 2,2-dialkyl-1,3-propanediol has a superior antiseptic effect and that it can be used as the effective ingredient of an antiseptic/antifungal agent. The inventors also discovered that an endermic liniment composition containing this antiseptic/antifungal agent has a superior antiseptic effect and that, even when the amount of parabens and/or phenoxy ethanol is substantially reduced, an anti septic properties adequate for normal use can be ensured. The inventors also discovered that, depending on the blend ratio of 2,2-dialkyl-1,3-propanediol, adequate antiseptic properties can be ensured in an endermic liniment composition without adding any parabens and/or phenoxy ethanol, thus completing the present invention.
That is, the present invention provides an antiseptic/antifungal agent in which 2,2-dialkyl-1,3-propanediol represented by the following general formula (I) is an effective component: 
[In this formula, R1 and R2 can either be identical or different from each other, and both denote an alkyl group with a carbon number of 1-4.]
Also, the present invention provides an endermic liniment composition which contains the antiseptic agent of the present invention (hereafter referred to as xe2x80x9cthe endermic liniment composition of the present inventionxe2x80x9d).
As mentioned above, in the endermic liniment composition of the present invention, it is possible to use 2,2-dialkyl-1,3-propanediol represented by general formula (I) as essentially the only antiseptic agent.
The inventors conducted the aforementioned research, and, as a result, discovered that, by blending a combination of 3-methyl-3-methoxybutanol, which has been widely used as a solvent for perfumes, and 2-phenoxy ethanol, which has been widely used as an antiseptic assistant, or 1,2-pentanediol, which has been widely used as a humectant, a surprisingly superior antiseptic effect is manifested and that antiseptic properties adequate for normal use can be ensured even if the blend ratios of parabens and/or phenoxy ethanol are significantly reduced. That is, although there have been examples of use of both of these compounds, they have not been used together, and the present invention discovered that the combined use of these compounds manifests a superior antiseptic effect and ensures the antiseptic properties.
The inventors discovered in particular that, depending on the blend ratios when combining 3-methyl-3-methoxybutanol and 1,2-pentanediol, adequate antiseptic properties can be ensured without using any parabens, and verified that usability and safety were excellent, thus completing the present invention. That is, the present invention provides an endermic liniment composition, such as various cosmetics, containing 3-methyl-3-methoxybutanol and 1,2-pentanediol or 2-phenoxy ethanol, which has superior antiseptic properties as well as superior usability and safety.
In this invention, xe2x80x9can endermic liniment compositionxe2x80x9d includes all compositions used for endermic use; for example it includes compositions which can be used widely in cosmetics such as foundation cosmetics, makeup cosmetics, hair cosmetics, etc. as well as in various drugs and/or quasi drugs such as ointments. The present invention also provides these modes of endermic liniment composition individually. In the present invention, xe2x80x9cantisepticxe2x80x9d means resistance against all contaminating microorganisms such as bacteria, fungi, yeast, etc., and xe2x80x9cantiseptic effectivenessxe2x80x9d means protection against all these contaminating microorganisms. Therefore, even when only the word xe2x80x9cantisepticxe2x80x9d is used in the present specifications, the concept of xe2x80x9cantimildewxe2x80x9d is not excluded.
Embodiments of the present invention are described below.
xe2x80x9cThe Invention Described in Claims 1-5xe2x80x9d
2,2-dialkyl-1, 3-propanediol which is used as an effective component of the antiseptic agent of the present invention is a neopentyl-type 1,3-propanediol represented by the above formula (I) hereafter this 2,2-dialkyl-1,3-propanediol (I) is also referred to as xe2x80x9ccompound (I)xe2x80x9d.
Different or identical alkyl groups with a carbon number of 1-4 which can be used for R1 and R2 include a methyl group, ethyl group, n-propyl group, isopropyl group, n-bbutyl group, isobutyl group, secondary butyl group, and tertiary butyl group.
Compound (I) is generally known as an prior art and has been disclosed in general engineering literature and/or patents in many forms. However, usually this is widely used as the raw material of urethane products and as a component of an insect repellent, and there has been no case where this was used as an effective component of an antiseptic agent.
Examples of compound (I) which are particularly superior in their antiseptic effect, less irritating, and superior in terms of usability of endermic liniments containing them include those whose R1 and R2 are a ethyl group, n-propyl group, isopropyl group, or n-butyl group (R1 and R2 can be either identical or different from each other). In particular, 2-n-butyl-2-ethyl-1,3-propanediol is easy to obtain and synthesize at the time of filing this application. Therefore, considering both the practical and economical aspects of implementation of the present invention, 2-n-butyl-2-ethyl-1,3-propanediol is superior as an effective component of the antiseptic agent of the present invention.
Compound (I) other than 2-n-butyl-2-ethyl-1,3-propanediol can also be prepared according to a prior art method, and such a product can be used for an effective component of the antiseptic agent of the present invention. Some examples of compound (I), including 2-n-butyl-2-ethyl-1,3-propanediol, are commercially available (products from Kyowa Hakko K.K., for example), and these commercial products can also be used as an effective component of the antiseptic agent of the present invention.
Compound (I) can either be used as it is for the antiseptic agent of the present invention or diluted/extended by using a diluent, filler or such.
As discussed later, compound (I) is preferably used in combination with propylene glycol and/or diols in an endermic liniment composition, and therefore both compound (I) and propylene glycol and/or diols (specific details will be given below) can be added to the antiseptic agent of the present invention. The form of the antiseptic agent of the present invention can be chosen as appropriate, as long as the effect of compound (I) in the original antiseptic agent of the present invention is not affected.
As described above, the antiseptic agent of the present invention with superior antiseptic effectiveness and superior safety is thus provided.
The endermic liniment composition of the present invention is an endermic liniment composition which contains the antiseptic agent of the present invention as described above.
The blend ratio of the antiseptic agent of the present invention in the endermic liniment composition of the present invention is, for full manifestation of the desired antiseptic effect in the endermic liniment composition, preferably 0.05 wt % or more, more preferably 0.5 wt % or more, in compound (I) equivalent, of the total amount of the composition (hereafter, the blend ratio of the antiseptic agent of the present invention will be expressed in compound (I) equivalent, unless specified otherwise). The antiseptic effect can be significantly increased by blending in 1.0 wt % or more of the total amount of the composition
When the blend ratio of the antiseptic agent of the present invention is 1.5 wt % or more, a superior antiseptic effect can be achieved essentially without using antiseptic components other than compound (I) which is an effective component of the antiseptic agent of the present invention such as paraoxy benzoate (commonly called parabens), salcylic acid and sorbic acid or antiseptic assistants such as phenoxy ethanol [xe2x80x9cessentially without using other antiseptic componentsxe2x80x9d means either antiseptic components other than compound (I) are not used at all, or the antiseptic effect of the other antiseptic component is latent in the endermic liniment composition (an example is a case when a compound which can be used for the other antiseptic component is used for a purpose unrelated to its antiseptic effect)].
The upper limit of the blend ratio of the antiseptic agent of the present invention in the endermic liniment composition of the present invention should not be limited in particular. However, usually if the blend ratio is more than 3.0 wt % of the total amount of the composition then the skin sensation at the time of use tends to become heavy; and if it is more than 10.0 wt %, then compound (I)""s characteristic odor becomes conspicuous and the quality of the endermic liniment composition tends to be degraded.
Also, diols such as propylene glycol, 1,3-butylene glycol, 1,2-pentane diol, dipropylene glycol, 1,2-butylene glycol, 2,5-hexane diol, 2,4-pentane diol, 2-methyl-2,4-pentane diol, 1,2-hexylene glycol, 1,6-hexylene glycol, and 1,5-pentane diol, of which the most preferable is 1,3-butylene glycol, can be used in combination with compound (I) in the endermic liniment composition of the present invention. In this case, even when the blend ratio of compound (I) in the endermic liniment composition is relatively low, adequate antiseptic properties are surprisingly ensured without adding antiseptic agents such as paraben or antiseptic assistants such as phenoxy ethanol, and an endermic liniment composition superior in both usability and safety is provided. Particularly, the endermic liniment composition of the present invention with this combination of components tends to be superior in usability and thus preferable. When this combination of components is used, the blend ratio of the aforementioned diol in the endermic liniment composition of the present invention is preferably 0.1-15 wt % of the total amount of the composition and 0.1-20 times (weight ratio) the amount of compound (I).
The present invention does not exclude the addition of other antiseptic components and/or antiseptic assistant components to the endermic liniment composition of the present invention as desired, even if compound(I) can provide adequate antiseptic effectiveness to the endermic liniment composition of the present invention and there is no need to add other antiseptic components and/or; antiseptic assistant components.
xe2x80x9c2: The Invention of Claims 6 and 7xe2x80x9d
(1) 3-methyl-3-methoxybutanol, which is one of the two essential components blended in the endermic liniment composition (hereafter referred to as xe2x80x9cthe present invention""s endermic liniment compositionxe2x80x9d), has a structure represented by the following formula. 
This compound is a component normally blended in an endermic liniment composition as one of the solvents of perfumes. It can be prepared with a common prior art method and blended in the present invention""s endermic liniment composition. Commercially available products (such as those from Kuraray Co., Ltd. ) can also be blended in the present invention""s endermic liniment composition.
The blend ratio of 3-methyl-3-methoxybutanol in the present invention""s endermic liniment composition is not limited in particular, and can be determined as appropriate depending on the required degree of antiseptic effectiveness and the blend ratio of 1,2-pentane diol which is used in combination with it. In order to effectively manifest the desired antiseptic effect in the endermic liniment composition, 0.1 wt % or more of the total composition is a preferable blend ratio. The upper limit of the blend ratio is not limited in particular; 10.0 wt % of the total amount of the composition is sufficient and no improvement in the effect can be expected by increasing it further.
(2) 1,2-pentanediol, which is another essential component to be blended in the present invention""s endermic liniment composition along with the aforementioned 3-methyl-3-methoxybutanol, is a compound with a structure represented by the following formula.
CH3(CH2)2CH(OH)CH2OH
This 1,2-pentanediol is a component normally blended in an endermic liniment composition as one of the humectants. For the 1,2-pentanediol to be blended in the present invention""s endermic liniment composition, those prepared with a normal prior method can be used. Commercially available products (such as those from DRAGOCO) can also be used.
The blend ratio of 1,2-pentanediol in the present invention""s endermic liniment composition is not limited in particular, and can be determined as appropriate depending on the required degree of antiseptic effectiveness and the blend ratio of 3-methyl-3-methoxybutanol which is used in combination with it. In order to effectively manifest the desired antiseptic effect in the endermic liniment composition, 0.1 wt % or more of the total composition is a preferable blend ratio.
The upper limit of the blend ratio of this 1,2-pentanediol should be decided as appropriate depending on the nature of the endermic liniment composition and should not limited in particular; 10.0 wt % of the total, amount of the composition is sufficient and no improvement in the effect can be expected by increasing it further. Blending 20.0 wt % or more of the total amount of the endermic liniment composition is not preferable because then the usability of the endermic liniment composition is affected due to stickiness and such.
For the relative blend ratio between the aforementioned 3-methyl-3-methoxybutanol and 1,2-pentanediol which are used in the present invention""s endermic liniment composition as an antiseptic means, it is preferable if the blend ratio of one is smaller when the blend ratio of the other is larger, or vice versa, for the purpose of effectively manifesting the intended effect of the present invention.
For example, as shown in Examples later, when the blend ratio of 3-methyl-3-methoxybutanol is 0.1 wt % or less (excluding 0 wt %) of the total amount.of the composition, the result is relatively good if 7.0 wt % or more of 1,2-pentanediol is blended in. When the blend ratio of 3-methyl-3-methoxybutanol is more than 0.1 wt % and 2.0 wt % or less of the total amount of the composition, the result is relatively good if 3.0 wt % or more of 1,2-pentanediol is blended in. When the blend ratio of 3-methyl-3-methoxybutanol is more than 2.0 wt % and 4.0 wt % or less of the total amount of the composition, the result is relatively good if 2.0 wt % or more of 1,2-pentanediol is blended in.
When the blend ratio of 3-methyl-3-methoxybutanol is more than 4.0 wt % and 7.0 wt % or less of the total amount of the composition, the result is relatively good if 1.0 wt % or more of 1,2-pentanediol is blended in. When the blend ratio of 3-methyl-3-methoxybutanol is more than 7.0 wt % and 10.0 wt % or less of the total amount of the composition, the result is relatively good if 0.1 wt % or more of 1,2-pentanediol is blended in.
(3) 2-phenoxy ethanol, which is another essential component to be blended in the present invention""s endermic liniment composition along with the aforementioned 3-methyl-3-methoxybutanol, is a compound with a structure represented by the following formula. This 2-phenoxy ethanol is a component normally blended in an endermic liniment composition as an antiseptic assitant. 
For the 2-phenoxy ethanol to be blended in the present invention""s endermic liniment composition, those prepared with a normal prior method, such as a method in which phenol is made to react with ethylene oxide or a method which uses a reaction between sodium phenoxide and ethylene chlorohydrine, can be used. Commercially available products can also be used.
The blend ratio of 2-phenoxy ethanol in the present invention""s endermic liniment composition is not limited in particular, and can be determined as appropriate depending on the required degree of antiseptic effectiveness and the blend ratio of 3-methyl-3-methoxybutanol which is used in combination with it. In order to effectively manifest the desired antiseptic effect in the endermic liniment composition, 0.01 wt % or more of the total composition is a preferable blend ratio.
The upper limit of the blend ratio of this 2-phenoxy ethanol should be decided as appropriate depending on the nature of the endermic liniment composition and should not limited in particular. One of the features of the present invention is that the blend ratio of 2-phenoxy ethanol can be reduced. Therefore, the blend ratio of 2-phenoxy ethanol is preferably small in consideration for some users who are sensitive to phenoxy ethanol, as long as the intended effect of the present invention is not affected.
For the relative blend ratio between the aforementioned 3-methyl-3-methoxybutanol and 2-phenoxy ethanol which are used in the present invention""s endermic liniment composition as an antiseptic means, it is preferable if the blend ratio of one is smaller when the blend ratio of the other is larger, or vice versa, for the purpose of effectively manifesting the intended effect of the present invention.
For example, as shown in Examples later, when the blend ratio of 3-methyl-3-methoxybutanol is 0.1 wt % or less (excluding 0 wt %) of the total amount of the composition, the result is relatively good if 0.5 wt % or more of 2-phenoxy ethanol is blended in. When the blend ratio of 3-methyl-3-methoxybutanol is more than 0.1 wt % and 1.0 wt % or less of the total amount of the composition, the result is relatively good if 0.3 wt % or more of 2-phenoxy ethanol is blended in. When the blend ratio of 3-methyl-3-methoxybutanol is more than 1.0 wt % and 3.0 wt %. or less, the result is relatively good if 0.1 wt % or more of 2-phenoxy ethanol is blended in.
When the blend ratio of 3-methyl-3-methoxybutanol is more than 3.0 wt % and 5.0 wt % or less of the total amount of the composition, the result is relatively good if 0.05 wt % or more of 2-phenoxy ethanol is blended in. When the blend ratio of 3-methyl-3-methoxybutanol is more than 5.0 wt % and 10.0 wt % or less of the total amount of the composition, the result is relatively good if 0.01 wt % or more of 2-phenoxy ethanol is blended in.
(4) As described above, according to the present invention, by using a new combination of 3-methyl-3-methoxybutanol and 1,2-pentanediol or 2-phenoxy ethanol, an endermic liniment composition can be provided which ensures adequate antiseptic properties and has both superior usability and safety, to our surprise, by using a small amount of 2-phenoxy ethanol without additionally blending in antiseptic agents such as parabens.
xe2x80x9c3: Common Descriptionxe2x80x9d
Depending on the specific embodiment of the endermic liniment composition, components normally blended in an endermic liniment composition can be blended into the endermic liniment composition of the present invention within the range which does not affect the expected effect of the present invention; such components include humectants, ultraviolet light absorbents, vitamins, animal/plant extracts, anti-inflammatories, whiteners, vasodilators, astringents, refreshers, and hormones.
As described above, the endermic liniment composition of the present invention can be used widely in product forms for application on skin such as cosmetics, drugs, and quasi drugs, and also a wide variety of formulations are possible, such as the aqueous solution system, solubilized system, emulsion system, oil-liquid system, gel system, paste system, ointment system, aerozol system, water-oil two layer system, water-oil-powder three layer system. That is, in terms of basic cosmetics, it can be used widely in the various formulations as described above and in forms such as a cleansing cosmetic, lotion, emulsion, cream, gel, essence, and pack/mask. In terms of hair cosmetics, it can be used widely in the various formulations as described above and in forms such as a shampoo, rinse, hair dressing, and hair restoration cosmetics.
In terms of drugs and quasi drugs, it can be widely used in the forms of various types of ointment, for example. Potential formulations and forms of the endermic liniment composition of the present invention are not limited to these formulations and forms.
Depending on the aforementioned desired formulations and forms, usual prior art base components can be widely blended in the endermic liniment composition of the present invention, as long as the expected effect of the present invention is not affected by this blending. That is, appropriate amounts of liquid fats/oils, solid fats/oils, waxes, hydrocarbon oils, higher fatty acids, higher alcohols, synthetic ester oils, silicones, various surfactants, sequestering agents, water soluble polymers, thickeners, various powder components, colorings, perfumes, and water can be blended as required into the endermic liniment composition of the present invention.